Incorporated as long ago as 1768, East Windsor is a little town on the east bank of the Connecticut River, composed of five villages.
There’s an intoxicating small-town charm to East Windsor, as well as some enlightening visitor attractions like a museum for electric railroading and a preserved academy building where some famous 19th-century Yale students got an education.
This is run by the local historical society, which takes care of a small campus of relocated landmarks.
In and around East Windsor are scenic walking trails, fruit farms, golf courses, craft breweries and antiques shops, while the New England Air Museum is a big regional attraction just across the river in East Granby.
Let’s explore the best things to do in and around East Windsor, Connecticut:
1. Connecticut Trolley Museum
East Windsor has what is thought to be the oldest museum for electric railroading in the United States.
The Connecticut Trolley Museum was set up in 1940 on the right of way of the Rockville Branch of the Hartford and Springfield Street Railway Company, which had been abandoned some 14 years earlier.
There’s a working 1.5-mile stretch of track, where you can take unlimited rides on restored streetcars from New Orleans, Montreal, Boston, Springfield, MA and around Connecticut.
At the visitor center’s main hall there are several static cars to check out, as you work your way through the history of this elegant mode of transport.
The museum is mainly a seasonal attraction open every day except Tuesdays between June and September, but there are special events at Halloween, Christmas and Easter.
2. Connecticut Fire Museum
In a warehouse to the rear of the Trolley Museum is a separate attraction dedicated to the history of firefighting in the state.
The museum has less frequent opening hours, so it’s worth checking in advance, but the good news is admission is included in the Trolley Museum ticket price.
What you’ll see is a rare repository of trucks and hand and horse-drawn firefighting equipment dating from 1850 to 1967. This is complemented by models and all sorts of memorabilia, from photographs to medals, historic life nets, flags, bells and uniforms.
3. East Windsor Academy Museum
The East Windsor Historical Society maintains a small handful of buildings at this campus in Scantic Village, but the most significant is this Federal-style academy building from 1817. Built with bricks on a brownstone foundation, the academy offered higher education to boys from the area, and among its alumni were Yung Wing (1828-1912), Yale’s (and America’s) first Chinese graduate and Junius Spencer Morgan (1813-1890), the banker father of J.P. Morgan.
By the middle of the 20th century the building had been converted into apartments, and was later bequeathed to the historical society by its owner.
Some of the intriguing things awaiting you inside are Native American arrowheads, a cannonball from King Philip’s War (1676), a scale model of the ferry that crossed the CT River from 1641 to 1917 and weapons, uniforms and other memorabilia from all of the nation’s wars.
4. East Windsor Hill Historic District
Mostly lining Main Street between the Scantic River and Edwards Cemetery is a historically important assemblage of folk vernacular buildings raised between the start of the 18th century and around 1860. This area, in the very north-west of East Windsor, was settled in the 1630s by families from across the river Windsor.
The two areas were connected by the Connecticut River’s first ever ferry, established in 1641. East Windsor families would have to cross the river to attend church until the General Court allowed them to found their own church society in 1691. In East Windsor Hill Historic District there’s a chronology of prevailing architectural styles from Georgian Colonial to Federal and Greek Revival, all designed by local architects.
What’s impressive is how much period detail remains.
The finest example of Georgian Colonial architecture is the Ebenezer Grant Mansion (1653 Main Street), while the standout Greek Revival building is the 1835 mansion commissioned by Bennett Tyler, the president of the Theological Institute of Connecticut (1748 Main Street).
5. St John’s Episcopal Church
A linchpin at Warehouse Point village, St John’s went up at the very start of the 19th century.
The curious story behind its foundation goes that some of the church’s founders were members of the First Congregational Church of East Windsor, who were keen to have a new church constructed.
This came about after the former meeting house burned down, and they were tried and acquitted of arson.
Outside the Episcopal Church is in the clean Federal style, with a two-stage tower and rows of Doric pilasters on the facade.
The interior meanwhile was reworked into a neo-Gothic style later in the 19th century, when the galleries to the side were taken down and a barrel vault was built over the nave, with a new chancel added at the rear.
6. Broad Brook Barber Shop Museum
Tucked behind the East Windsor Academy is a set of smaller buildings, each with its own tale to tell.
The Barber Shop dates from the end of the 19th century and was moved here from Broad Brook in 1967. From the 1880s this was the business of one Maximilian Ertel, a Saxony native who sold the shop to the local judge Rudolph C. Geissler in 1919. Inside are interesting artifacts like Ertel’s license and Geissler’s actual barber chair.
Another pocket-sized 19th-century building on the site is the East Windsor District Probate Court, also used for a time as a doctor’s office in the 1860s, while there’s a collection of farming equipment in what was once a tobacco shed, and along Scantic Road is the recently restored Osborn House (1785).
7. Scantic River State Park
This linear park is in different sections adding up to almost 800 acres and lining the banks of the Scantic River in East Windsor, Enfield and Somers.
The park was in the pipeline for 20 years after first being planned in the 1960s, and has grown steadily over the last 20 years.
So far about a third of the planned 2,200 acres have been acquired.
In East Windsor there’s an access point at the very end of Melrose Road in Broad Brook.
It’s all a very pretty place to go for a hike, with low, rolling hills, riverbanks in hardwood forest and a stretch of rapids with a little waterfall.
Near the trailhead by the parking lot you’ll come to the eerie remains of a steel-frame bridge over the river.
8. Problem Solved Brewing Company
Throw a dart at a map of Connecticut and there’s a good chance you’ll hit a craft brewery.
The fierce competition means that only the best survive, and that applies to East Windsor’s Problem Solved Brewing Co., which has a high rating on the notoriously competitive Untappd.
Problem Solved focuses its energy on a small line-up: The draft list in October 2019 consisted of just five beers, including Prime Factor, a Belgian saison, Second Root, a cream ale with coffee, Conductivity, a centennial IPA, The Origin, a sweet wheat stout and One Squared, a red honey lager.
New beers are released every few weeks, so there will always be something different.
There’s always one or two guest ciders on tap as well, and you can bring your own food or get a takeout delivered, and take on friends at a board game.
The taproom is open Thursday to Sunday.
9. East Windsor Park
Clean and well-maintained, East Windsor Park is a typical recreation space, with lighted basketball and tennis courts, a volleyball court and a sizeable playground for wee ones.
Where the park stands out is for the Broad Brook Reservoir, which serves as a swimming area in the summer months and is fitted with a slide and diving board.
There’s a nice patch of sand beside it, and children will have a fun time playing and building sand castles.
A concession stand is open at this time, and there are grills as well as two pavilions that can be rented by residents.
When we made this list in 2019, non-residents could visit only Monday to Thursday in summer.
10. New England Air Museum
A mere 10 minutes from Warehouse Point is the region’s premier aviation museum in a set of three hangars at Bradley International Airport.
With a staggering fleet of historic aircraft, the museum charts New England’s contribution to America’s aviation industry, paying special attention to Connecticut brands like Sikorsky, Kaman and Pratt & Whitney.
You’ll get to see the oldest surviving Kaman and Sikorsky aircraft, a K-225 and an S-39, as well as the last remaining Sikorsky VS-44A flying boat.
Also relevant to this state is the display for the balloonist Silas Brooks (1824-1906), whose preserved basket here is thought to be the oldest surviving aircraft in the entire country.
The museum’s informative displays are as interesting as the aircraft and dive into topics like the Wright Brothers, New England Women in Aviation, Sikorsky and Pratt & Whitney.
11. The Vintage Shops
Part of the joy of this antiques center in Warehouse Point is its location, in a stately Greek Revival-style building with a bold portico.
There are 11 different dealers in this space, all with a slightly different speciality.
Airwaves Antiques for instance deals in vintage radios, amongst other things, while the Clock Man sells timepieces going back to the 1700s.
Reflections of the Past meanwhile as a bit of everything, be it coins, kitchenalia, ephemera, political artifacts or lighting.
As for the building, this has had a few different uses down the years, as a boarding house and later a bar.
12. Grassmere Country Club
For a high-quality round of golf you won’t have to travel further than this public course five minutes away in Enfield.
Grassmere Country Club has a nine hole course that opened in 1973 and includes a practice green and chipping green.
Things start off tricky as the first two holes have doglegs (both par 4s), and the fourth hole (also par 4) isn’t much easier for its long, blind uphill second shot.
The fifth (par 3) is a favorite for its distant view to the green, but a winding brook comes into play here and on the par 3 ninth, which has a treacherous sloping green.
13. Windsor Locks Canal State Park Trail
Hop across the Connecticut River and you can take an easy waterside walk on a trail steeped in history.
This 4.5-mile walk is on the towpath of the Enfield Falls Canal, which was built in the 1820s to help waterborne traffic avoid a difficult piece of the Connecticut River.
Until the days of the canal, boats would require the services of a fallsman, propelling the craft with set poles.
The canal was quickly redundant as a means of transport thanks to the arrival of railways, but soon found another use as a supply for water-powered mills.
As well as granting uplifting views of this famous river, the trail has lots of 19th-century stonework leftover from the canal, in the form of bridges and aqueducts.
14. Warehouse Point Library
East Windsor’s local library punches above its weight for a town of this size.
Beyond its books, movies and other media, the Warehouse Point Library is a pillar of the community, organizing clubs, activities and classes for all ages, as well as weekly screenings of recent movies and exhibitions by local artists and photographers.
If you’re a non-resident just visiting, the library can be very handy in a pinch.
You can make use of the free Wi-Fi and public computers, bury your head in a book, newspaper or magazine for an hour or two, and pick up any information you might need about East Windsor and its surroundings.
15. Irish Bend Orchard
Just outside the East Windsor village of Melrose is a quintessential New England fall attraction.
The pick-your-own season at Irish Bend Orchard lasts from August to October, beginning with peaches and nectarines, followed by Asian pears and ending with a host of apple varieties.
You can also drop by the farm stand, which stocks all of this produce.
Towards the end of autumn is time for pumpkins, when children will be able to go on free hayrides on weekends.
There’s a convenient guide on the farm’s website letting you know what’s in season.